Dimethyl Sulfoxide → HCID 86756330, 화합물

HRID 568290노트

반응식

HRID 568290 반응식
CC(C)([O-])C.[K+].[Cl-].[S:8]1[CH:12]=[CH:11][N:10]2[C:13]([CH2:16][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[N:14][CH:15]=[C:9]12.[CH2:36]([O:39][C:40]([N:42]1[C@H:46]([CH:47]=O)[CH2:45][C@@H:44]([O:49][Si](C(C)(C)C)(C)C)[CH2:43]1)=[O:41])[CH:37]=[CH2:38].C(OCC)(=[O:59])C.C[S:64]([CH3:66])=[O:65]>C1COCC1>[CH2:36]([O:39][C:40]([N:42]1[C@H:46]([CH:47]=[CH:16][C:13]2[N:10]3[C:9]([S:8][CH:12]=[CH:11]3)=[CH:15][N:14]=2)[CH2:45][C@@H:44]([O:49][S:64]([CH3:66])(=[O:59])=[O:65])[CH2:43]1)=[O:41])[CH:37]=[CH2:38]

참가 물질

7

반응물 5

HCID 679Dimethyl SulfoxideHCID 8857Ethyl AcetateHCID 21262400HCID 21262400, 화합물HCID 22870383(2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-formylpyrrolidineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 86756330HCID 86756330, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Potassium t-butoxide (0.11 g) is added to a solution of 0.44 g of (imidazo[5,1-b]thiazol-5-yl)methyltriphenylphosphonium chloride in 2 ml of THF and 2 ml of dimethyl sulfoxide under ice cooling. The mixture is stirred at that temperature for one hr, and a solution of 0.28 g of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-formylpyrrolidine in 2 ml of THF, and the mixture is stirred at that temperature for 2 hr. Ethyl acetate is added to the reaction mixture, and the mixture is successively washed with dilute hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and saturated saline and dried over anhydrous magnesium sulfate. The solvent is removed by evaporation, and the residue is purified by column chromatography on silica gel (methanol:ethyl acetate=5:95) to give 0.33 g of (3R,5S)-1-allyloxycarbonyl-5-[2-(imidazo[5,1-b]thiazol-5-yl)ethenyl]-3-methanesulfonyloxypyrrolidine (a mixture of geometrical isomers).

후처리

  1. washthe mixture is successively washed with dilute hydrochloric acid
  2. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated saline and dried over anhydrous magnesium sulfate
  3. customThe solvent is removed by evaporation
  4. customthe residue is purified by column chromatography on silica gel (methanol:ethyl acetate=5:95)

출처 및 근거

ORD 기록
ord-926aefcf4dd04b8a8d2dcd8d37ed5b94
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180622B2

반응 노트

불러오는 중…